As far as rentals, I look for Multi-family properties that are in good shape and in need of only light to moderate work between tenants.  

If it's moderately to highly distressed then we will usually get a GC to give us a better idea on budget though.

I'll work on that one thing nonstop, day and night and then i'll just get bored with it and move on. for instance, right now i'm rebuilding/chopping my harley, taking guitar lessons online, moderating the guitar site messageboard, learning to train my pitbull , studying the feasibility of constructing a supercross track in my area, and of course learing the in's and out of real estate and thats just in this month alone.

It is all in need of extensive rehab work if you want to put things on the retail market, but only requires moderate rehab for a buy and hold.  

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Fifty cents on the dollar for a good home that needs moderate repair.

A big part of that thanks has to go out to @Jon Holdman the OG moderator for the site.

Housing is so critical, Disney just recently announced they are setting aside 80 acres for moderately priced housing to be built probably targeting the lower paid workers who work at Disney. 

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By the way, Chicago is a great market, one of our other moderators @Steven Hamilton II is active there.